


For the Lackadaisy. At least at first anyway.

by Anonymous



Category: Lackadaisy (Webcomic)
Genre: Anal Fingering, Anal Sex, M/M, Oral Sex, Prostitution, Rimming
Language: English
Status: Completed
Published: 2021-01-19
Updated: 2021-01-19
Packaged: 2021-03-17 09:01:17
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,604
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28846458
Author URL: https://archiveofourown.org/
Summary: Rocky is given an offer he could have refused. But he figures what the hell and takes the opportunity for a quick dollar.
Relationships: Rocky Rickaby/ Original Character
Kudos: 4
Collections: Anonymous





	For the Lackadaisy. At least at first anyway.

Rocky hums as he plays his violin. He has the day off and the sun is shining so he figured, why not go busking in the park?

Anything to help his current business venture and keep him from living with the hobos and hopping trains. He's already made a few dollars today and every penny counts.

A man is casually walking over to him. Tall with light brown fur and a very handsome face. Dressed in some very fancy clothing that just scream money.

"Hello sir, you play very well" he spoke politely.

Rocky gave a small smile "Why thank you, I do try to get in a bit of practice when I can" he responded.

He isn't sure what this guy is after, but he's curious by nature. So he will play nice for now. "Any song requests?" He prompted

The man chuckled, deep brown eyes filled with mirth "Ah, no. I'm okay, I have a different offer though. How would you like to make fifty dollars?"

Rocky went wide eyed but quickly bit his tongue. Can't say yes right away, he learned that lesson the hard way. "Well, most people would, but it does depend on the job on how willing I would go along."

The man's smile is amused and he stepped a little closer. "You see my friend I am a man who rarely can truly enjoy himself the way I would wish to. Being the rich and affluent man I am I was forced to take a wife. One I never would have had be I a commoner you see"

Rocky is now very much aware what the handsome stranger is interested in. Himself. Wide eyed he stares at him in surprise. Feeling a little suspiciously warm over it.

"I understand if you decline you know. I won't be offended." The rich gentleman says after Rocky's hesitation.

Rocky shook his head to snap himself out of his own thoughts. He looks over the stranger and weighs the pros and cons. He never figured himself into men but he isn't bad looking. Rather attractuve actually. And the Lackadaisy could use the money. He played the scenario a number of different ways in his head and figures selling his body is still not the worst thing he's done in life.

"Well I could be agreeable, I just never been offered or thought about this situation before. Besides what is life without adventure? Variety and change is what gives our mortal time it's flavor and entertainment after all. So O' handsome gentleman your tale of woe has filled my ears and moved my heart. Whisper to me your secret desires and we shall make a deal"

The well dressed man snorted. The musician moved as fluidly as he spoke. Truly a performer but it did make him wonder. "Are you sure you have never considered my kind of company before? That was quite the performance." He teased.

Rocky was again thrown off balance. He recovered quick enough though. "As sure as I can be. However I do understand the misunderstanding, many a performer like myself are like you, or at least mistaken as. I'm Rocky, and you are?"

He held out a hand, the man took it and gave a firm shake. "Henry, a pleasure Rocky" Henry introduced himself

"Hmm not yet at least. So do you have a venue already planned?" Rocky asked

Henry snickered at the sly cats words "The wife won't be home for a week. So I can bring you to my home and we can enjoy ourselves uninterrupted"

Rocky nodded and walked after Henry following him home. They managed to talk casually on the walk there. Henry is actually very nice in general. Him and Rocky getting on well already.

Henry finds himself charmed by the high energy whimsy that Rocky gives off, all with that signature grin of his. He can't help but imagine a little the idea of keeping him around.

Rocky likes the relaxed nature of the man he's walking with. Confident yet considerate. He feels they will get along great, even though he's about to do things to his butt.

A first certainly, but he can deal with it for the cash he's getting. It'll make Mrs. May happy to have some extra cash laying around. Idly he wonders what normal working gals and guys make and just how far he could potentially make this work.

Especially if he's able to get ladies to buy his services. Get laid and paid? Yes sir. So depending on how well this goes he may have a side business.

Henry is a lot more wealthy than Rocky originally thought. Because he has one very large mansion behind a very large and fancy gate. He internally guesses correctly that the fifty dollars although big for him is nothing but a drop in the bucket for Henry.

The inside has beautiful wood floors, soft red carpets, beautiful art along the walls, and fancy wallpaper. A true display of decadence. He figures if Henry tries to pull anything funny he can just snag a couple of trinkets and make more than he was offered.

The door closed and Henry looked at him very warmly. "I would like to kiss you if that's alright?" Henry says.

Rocky gulped but nodded. The man's arms wrapped around him pulled him close and stared right into his eyes. Rocky can feel his cheeks heating up and closes his eyes. He leans in and Henry met him halfway.

Rocky allows himself to melt into it and kiss back. A small hum of enjoyment escaping past his lips. Tongue was introduced and he actually moaned. Henry is a good kisser and his previous concerns about not having a good time doing this are melting away with each caress of their lips.

Pulling away to breathe Henry's eyes are dark with lust and Rocky feels genuine attraction. He is lead up a grand staircase and to a very well furnished bedroom.

Large bed with the tall bed posts and curtains around it deep red sheets and pillows, and a soft mattress. There's an oak writing desk and a fireplace as well as a large set of drawers and a closet. He's also certain the door at the back right corner leads to a bathroom.

Henry looks right into his eyes again and starts undoing the buttons to his coat. "Now if anything feels too uncomfortable just say so and we can compromise. But until then, start stripping"

Rocky doesn't think he has ever been so quick to start undressing for someone. And he will admit during his travels there were a number of beautiful ladies he was glad to strip for.

He joined Henry on the bed sharing a few small kisses as any leftover clothes were tossed. Henry pushed Rocky to lay on his back. The man kissed his way down Rocky's body. Nibbling at his neck. Teasing the little pink nubs hiding beneath his fur then down to his thighs purposefully avoiding the growing member between his legs.

"So cute" Henry muttered and then he took in the tip into his mouth.

"Oh fuck" Rocky cursed as that wet heat enveloped him.

Henry gently began to suck and lick over his now erect penis bobbing his head. Rocky squirming under his touch turning him on. He looks up at him and Rock shuddered.

The way those eyes looked right through him as he sucks him so lustfully amplifies the sensation for Rocky. He gasps Henry's name and a hand landed on the gentleman's head.

Henry teased him stopping and starting to keep him on edge. As fun as making him cum now would be he wants to wait.  
Rocky feels so hot right now, like liquid fire is coursing through his veins.

"Flip over and I'll show you something else that feels good" Henry says darkly.

Rocky rolls over and presents his ass too turned on to feel worried about what's coming next. Strong confident hands grab his cheeks and spread them.

Henry loves Rocky's ass already. A lovely round shape, full and fills his hands, soft but firm, and a cute pink opening. He's sure Rocky would never have even heard of what he's about to do.

Rocky was about to ask what Henry is going to do as the man licked a stripe from his balls and all the way up lapping over his asshole. The noise that escaped him was different than any other moan he has made in his life. Much like the electric jolting pleasure he just felt.

Henry put his face right in and licked and lapped all over his pucker. Kissing and sucking the opening listening to the erotic music Rocky is making.

This is the best Rocky has ever felt in his opinion. The feeling is so demanding it spreads through his ass right to the tip of his now leaking erection, and then tremors through his whole body. He felt he could cum from the first few licks but now he's barely holding on as he squirms under this man's touch. Then the tongue actually went inside. Had he not gasped so hard the scream that escaped past his lips wouldn't be as silent or strangled.

"Oh yes! Henry!" Rocky cried pushing back into the tongue begging for more.

Henry was happy to make out with his hole another few moments. He has to still stretch him however and get him ready for what's to happen.

He throbbed at the whine Rocky made when he stopped to grab lube. "Henry" he made such a desperate sound.

It took restraint not to just put it in hearing that. But Henry held back and slicked up his fingers. He circled a single digit around the rim and then let it slip right in.

Rocky once again was surprised by how much he is enjoying the new sensation he's being introduced to. The strange new filling sensation that stretches out his inner walls. Henry keeps his ass up grabbing the base of his tail firmly as finger number two pushed in with the first. Spreading apart as well as in and out.

The stretch has his mind go blank. A mix of burning pain and pleasure, and he wants more. Finger number three opens him up enough for Henry to find the spot that makes Rocky scream.

Henry expertly rubbed the cats prostate and listens to the broken begging he makes to let him cum! To fuck him already!

Henry has Rocky rolled onto his back. He wants to watch the cat fall apart as he fucks him. But first he crawled up and rested his knees on either side of Rocky's chest "I want you to show me how much you want it" Henry purred his cock hovering just over over the man's face.

Rocky opens his mouth gladly. One advantage of having such a big mouth Henry was able to put it right in. He lifts his head to take in more sucking on the stiff flesh. Henry groans and tries not to immediately buck his hips and fuck his face.

Rocky notices immediately that a mans sex has a very different taste than a womans. He finds he likes it and that he isn't gagging thankfully. Henry, Rocky noticed, is even longer than him and a bit thicker too. So the fact the other man's balls are resting on his chin is a rather big accomplishment for a first time.

"Oh wow! You're already so good!" Henry praised. He started to move his hips on his own. The musicians deep blue eyes looking up at him his soft lips clamping around the dick.

"Such a good boy" Henry grumbled

Rocky at this moment feels his body heat up a little more and his dick throb. His tail also starting to swish against the bed. It appears he likes being complemented in bed.

With a wet pop Henry pulled out of Rocky's mouth and lathered himself with a healthy covering of lube and positioned himself between Rocky's legs. The tip just touching the entrance.

"Ready for me?" Henry's question spoken breathelly

Rocky nods quickly and opens his arms and legs meaningfully. Henry pushed very slowly inside careful not to hurt him. The tip popped in and Henry was able to sink in halfway before stopping.

Rocky made an odd noise. Inbetween a yelp and a moan. Dicks, he just learned, are a lot thicker than fingers. He feels so full already and it's rubbing against his deepest insides. The pressure just a small hair away from that spot Henry made him see stars with earlier.

He took a deep breath and as he let it out trying to stay relaxed another bit of Henry sank in and is now resting heavy against his prostate. "Oh fuck! S-s-so bi-big!" He moaned.

Henry is no better off. Rocky has somehow the tightest but softest ass he has ever had the pleasure of being inside of. The heat all around his tool is maddening and he wants nothing more than to feel it milk his cock. He grits his teeth and moves slowly. He grips the man beneath him and held him close.

"You feel amazing" Henry spoke just above a whisper right into his ear. There's a gasp and the walls clench around him. It nearly halts the slow methodical rocking of his hips. Gradually putting more and more of himself inside.

Rocky felt the firm smack of the man's hips connecting with his ass. Feeling stuffed to the limit, he groans and his grip on the man above him gets tighter grabbing and scratching at his back as the pace picks up momentum. His legs by instinct wrap around Henry's hips trying to buck himself on the cock that's invading him.

The inside of his head is foggy he only feels Henry inside and out and the soft cradle of the bed below. Only hears them moaning and the clap of their bodies colliding. This one instance becoming his whole world as that building coiling pressure of orgasm rises from deep inside and is clawing it's way to the surface. It's rough and raw like Henry's thrusts are getting. He's not going to last, any moment this man is going to make him cum from a hard fucking he didn't even know he wanted until today.

Henry is not far behind the embrace of Rocky's body is the best he has ever had. The man he's inside is everything he's always wanted and more. The way he walks, talks, the sounds he's making all wrapped up in this charmingly cute package.

"Clo-aaah! Close! I'm! Nngaah!" Rocky cried.

His vision cut off completely the coil snapped and his cum jetted out of his pulsing member one shot after another like a sticky shot gun his whole body shaking with the force of it in toe curling bliss.

The rapture on his face and the way he clamped and spasmed had Henry's hips stutter and he stiffened up and exploded inside. He thrusted his way through his climax making sure to get all he can out of it for the both of them.

The hot rush of cum inside him made Rocky feel oddly happy. Warm inside and out as Henry and he pant for breath the other man now laying on him and holding him close.

He eventually slipped out and moved to lay beside Rocky and held him to his chest. He cuddled back and let himself drift off. He can deal with the mess and any soreness later.

He woke up later to still being in Henry's arms. The man softly scratching the spot right behind his ear. He purred lightly and snuggled a little tighter. "Keep treating me so kind I may just never leave" Rocky spoke, sunny in tone.

"Mmm, I was thinking of offering you a little extra to stick around a couple days. The wife won't be back for a while and I rather enjoyed the time we've spent together" Henry responded.

"Don't have to pay me any extra for me to stay if you want. That was the best sex I ever had" Rocky admitted.

"Speaking of, we should get cleaned up. A hot bath and all that" Henry suggested

The hooch peddler agreed and let himself be carted off to the bathroom. He was a little sore and had a bit of trouble walking but Henry was happy to help.

Rocky spent the next two days living in a strangely domestic situation with Henry and a promise to meet again when he left.

'Wait... Did I just make a married man my boyfriend?' he wondered to himself. All the sex, the cuddling, sharing food, and the kisses all through his time there replayed in his mind. Then the way Henry kissed him before he left making Rocky promise to come back some day as he gave him an envelope with the money in it.

He realized that's exactly what he did. Still not the worst thing he's done, but he does feel bad for the wife. Henry said she's aware of his interests but he isn't sure how that works between them. He's worried about lighting a powder keg here.

He waltzed into the cafe on some still wobbly legs. "Good afternoon everyone!" He cheered to those sitting around.

"Heya Rocky you disappeared for like, three days. Where were you?" Ivy asked.

"I was off galavanting with the social elite Miss Pepper. I met a rich type that liked my violin mastery and took me home and sent me off with this here bundle. All in a days whimsy for the sweet Lackadaisy" he waved the envelope of money.

Calvin tilted his head and looked to his girlfriend. "Even I can't translate that one" he says with a shrug.

Mitzi who was leaning against the counter sighed "He was busking in the park when someone offered him money for his body. He's been playing gigolo with someone rich, and judging by the funny walk it was a man... Or an adventurous woman with a marital aid at least" 

Ivy went red in the face while Calvin choked on the sandwich he was eating. His lady thumped him on the back and got him stable again.

"I'm s-sorry bu- *hack* y-you d-did what?" He spoke still coughing.

"Exactly as Miss M. Said. A rich person wanted me, I obliged for monetary gain. Fun time, would certainly do it again"

"She also brought up roundaboutly things were done to your butt" Ivy drawled

Calvin's head met the table blushing madly. He has always been rather sensitive to adult topics.

"Astute observation Miss Pepper. Sharp as always. And yes they did. I actually learned a lot because of that. One, that there's a place inside men that can make you see paradise when touched right, and two, that even if you don't like things going in there if you're partner offers to lick it absolutely say yes." Rocky spoke raising a finger for each point.

"So was this rich person a man or a woman?" Ivy questioned trying not to get ideas.

Calvin still went a little stiff where he sat. Rocky at times wonders if the boy is psychic.

"My company was male and I must say the experience was very eye opening. Now before I forget" Rocky put down the envelope infront of Mitzi.

The woman opened it and her eyes went wide. "Holy crap! He gave you a hundred dollars?!" She shouted

"What?! He did?! Man and I agreed at fifty. Oh man, I... He must have really liked me" Rocky for once is at a loss for words.

"Rocky who the hell were you screwing?!" Ivy demanded

"Henry, uhh, Henry... I actually don't know his last name. Just that I'm seeing him again in a couple days. Ya know... For a date"

"Too busy to ask questions?" Ivy teased

"Hard to talk when your mouth is full anyway" he crassly teased back 

"Wait... does he have brown fur and eyes? Dress real fancy?" Calvin asked

"You know him?" Rocky responded

"No but his picture is in the paper with an article written about him. Henry Wells oil tycoon. Age 29 married with no current children" Calvin spoke and showed the image.

"Yup, that's him alright. Camera only does him half justice. He's much better looking in person" Rocky confirmed

"Married? Really Rocky?" Ivy comments

"Hey now! Only because he had to be. Also he says his wife is very aware of his tastes. As long as he hides it from the public and doesn't flaunt it too much around her he's free to have all the pretty boyfriends he wants."

"This I've seen before" Mitzi said "Not the accepting your husband's lovers part, but certainly the heir to a wealthy family expected to marry a woman and continue the bloodline and the company part."

This lead to a philosophical discussion on the basis of marriage. Things tapered off and Mitzi gave half of it back to Rocky. He would have let her keep the whole hundred but he earned it in her mind.

She did warn him to do his damnedest to avoid a scandal. "Who me? Why Miss M. You know I'm not one for scandal. A little running and gunning sure but scandal? You wound me madam" 

"Look I know I just jinxed it but at least do your best when the shit hits the fan?" She says with a tired smile

"For you Miss M. Always."


End file.
